US8865699B2ActiveUtilityPatentIndex 55
Amino triazoles as PI3K inhibitors

Assignee: RAMSDEN NIGELPriority: Nov 27, 2007Filed: Nov 21, 2008Granted: Oct 21, 2014
Est. expiryNov 27, 2027(~1.4 yrs left)· nominal 20-yr term from priority
Inventors:RAMSDEN NIGEL BELL KATHRYN CANSFIELD ANDREW DAVID TAYLOR JESS SUNOSE MIHIRO MIDDLEMISS DAVID NEUBAUER GITTE
A61P 9/00A61P 37/02A61P 37/00A61P 3/10A61P 43/00A61P 37/08A61P 37/06A61P 35/00A61P 3/00A61P 25/00A61P 25/28A61P 27/16A61P 31/00A61P 29/00A61P 27/02A61P 11/00A61P 19/06A61P 17/06A61P 17/00C07D 471/04A61P 1/18A61P 11/06A61P 1/00A61P 19/02A61P 1/04
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References
Claims
Abstract

The invention relates to compounds of formula (I) wherein X, T 1 and R 1 to R 3 have the meaning as cited in the description and the claims. Said compounds are useful as protein kinase inhibitors, especially inhibitors of PI3K, for the treatment or prophylaxis of immunological, inflammatory, autoimmune, or allergic disorders. The invention also relates to pharmaceutical compositions including said compounds, the preparation of such compounds as well as the production of and use as medicaments.
Claims

exact text as granted — not AI-modified
The invention claimed is: 
     
       1. A pharmaceutical composition comprising a compound of formula (I) 
       
         
           
           
               
               
           
         
         or a pharmaceutically acceptable salt thereof, wherein 
         X is NH 2 ; 
         R 1 , R 2 , R 3  are independently selected from the group consisting of H; halogen; CN; C(O)OR 4 ; OR 4 ; C(O)R 4 ; C(O)N(R 4 R 4a ); S(O) 2 N(R 4 R 4a ); S(O)N(R 4 R 4a ); S(O) 2 R 4 ; S(O)R 4 ; N(R 4 )S(O) 2 N(R 4a R 4b ); N(R 4 )S(O)N(R 4a R 4b ); SR 4 ; N(R 4 R 4a ); OC(O)R 4 ; N(R 4 )C(O)R 4a ; N(R 4 )S(O) 2 R 4a ; N(R 4 )S(O)R 4a ; N(R 4 )C(O)N(R 4a R 4b ); N(R 4 )C(O)OR 4a ; OC(O)N(R 4 R 4a ); and C 1-6  alkyl, wherein C 1-6  alkyl is optionally substituted with one or more halogen, which are the same or different; 
         R 4 , R 4a , R 4b  are independently selected from the group consisting of H; and 
         C 1-6  alkyl, wherein C 1-6  alkyl is optionally substituted with one or more halogen, which are the same or different; 
         T 1  is 4 to 7 membered heterocyclyl; 9 to 11 membered heterobicyclyl; phenyl; naphthyl; indenyl; or indanyl; wherein T 1  is optionally substituted with one or more R 5  and/or one or more R 6 ; 
         R 5  is halogen; CN; C(O)OR 7 ; OR 7 ; oxo (═O), where the ring is at least partially saturated; C(O)R 7 ; C(O)N(R 7 R 7a ); S(O) 2 N(R 7 R 7a ); S(O)N(R 7 R 7a ); S(O) 2 R 7 ; S(O)R 7 ; N(R 7 )S(O) 2 N(R 7a R 7b ); N(R 7 )S(O)N(R 7a R 7b ); SR 7 ; N(R 7 R 7a ); OC(O)R 7 ; N(R 7 )C(O)R 7 ; N(R 7 )S(O) 2 R 7a ; N(R 7 )S(O)R 7a ; N(R 7 )C(O)N(R 7a R 7b ); N(R 7 )C(O)OR 7a ; OC(O)N(R 7 R 7a ); or C 1-6  alkyl, wherein C 1-6  alkyl is optionally substituted with one or more R 8 ; 
         R 6  is T 2 ; C(O)OR 9 ; OR 9 ; C(O)R 9 ; C(O)N(R 9 R 9a ); S(O) 2 N(R 9 R 9a ); S(O)N(R 9 R 9a ); S(O) 2 R 9 ; S(O)R 9 ; N(R 9 )S(O) 2 N(R 9a R 9b ); N(R 9 )S(O)N(R 9a R 9b ); SR 9 ; N(R 9 R 9a ); OC(O)R 9 ; N(R 9 )C(O)R 9a ; N(R 9 )S(O) 2 R 9a ; N(R 9 )S(O)R 9a ; N(R 9 )C(O)N(R 9a R 9b ); N(R 9 )C(O)OR 9a ; OC(O)N(R 9 R 9a ); or C 1-6  alkyl substituted with one or more T 2  and optionally substituted with one or more R 8 ; 
         R 9 , R 9a , R 9b  are independently selected from the group consisting of R 9c ; and R 9d , provided that at least one of R 9 , R 9a , R 9b  is R 9c ; 
         R 9c  is T 2 ; or C 1-6  alkyl, wherein C 1-6  alkyl is substituted with one or more T 2  and optionally substituted with one or more R 8 ; 
         R 7 , R 7a , R 7b , R 9d  are independently selected from the group consisting of H; and C 1-6  alkyl, wherein C 1-6  alkyl is optionally substituted with one or more R 8 ; 
         R 8  is halogen; CN; C(O)OR 10 ; OR 10 ; C(O)R 10 ; C(O)N(R 10 R 10a ); S(O) 2 N(R 10 R 10a ); S(O)N(R 10 R 10a ); S(O) 2 R 10 ; S(O)R 10 ; N(R 10 )S(O) 2 N(R 10a R 10b ); N(R 10 )S(O)N(R 10a R 10b ); SR 10 ; N(R 10 R 10a ); OC(O)R 10 ; N(R 10 )C(O)R 10a ; N(R 10 )S(O) 2 R 10a ; N(R 10 )S(O)R 10a ; N(R 10 )C(O)N(R 10a R 10b ); N(R 10 )C(O)OR 10a ; OC(O)N(R 10 R 10a ); or C 1-6  alkyl, wherein C 1-6  alkyl is optionally substituted with one or more halogen, which are the same or different; 
         R 10 ; R 10a ; R 10b  are independently selected from the group consisting of H; and C 1-6  alkyl, wherein C 1-6  alkyl is optionally substituted with one or more halogen, which are the same or different; 
         T 2  is C 3-7  cycloalkyl; 4 to 7 membered heterocyclyl; 9 to 11 membered heterobicyclyl; 
         phenyl; naphthyl; indenyl; or indanyl, wherein T 2  is optionally substituted with one or more R 11 ; 
         R 11  is halogen; CN; C(O)OR 12 ; OR 12 ; oxo (═O), where the ring is at least partially saturated; C(O)R 12 ; C(O)N(R 12 R 12a ); S(O) 2 N(R 12 R 12a ); S(O)N(R 12 R 12a ); S(O) 2 R 12 ; S(O)R 12 ; N(R 12 )S(O) 2 N(R 12a R 12b ); N(R 12 )S(O)N(R 12a R 12b ); SR 12 ; N(R 12 R 12a ); OC(O)R 12 ; N(R 12 )C(O)R 12a ; N(R 12 )S(O) 2 R 12a ; N(R 12 )S(O)R 12a ; N(R 12 )C(O)N(R 12a R 12b ); N(R 12 )C(O)OR 12a ; OC(O)N(R 12 R 12a ); or C 1-6  alkyl, wherein C 1-6  alkyl is optionally substituted with one or more halogen which are the same or different; 
         R 12 ; R 12a , R 12b  are independently selected from the group consisting of H; and C 1-6  alkyl, wherein C 1-6  alkyl is optionally substituted with one or more halogen, which are the same or different, together with a pharmaceutically acceptable carrier. 
       
     
     
       2. A pharmaceutical composition according to  claim 1 , wherein R 1  and R 2  are independently H or CH 3 . 
     
     
       3. A pharmaceutical composition according to  claim 1 , wherein R 3  is H, CH 3  or halogen. 
     
     
       4. A pharmaceutical composition according to  claim 1 , wherein T 1  is unsubstituted phenyl; substituted phenyl; unsubstituted 4 to 7 membered heterocyclyl; substituted 4 to 7 membered heterocyclyl; unsubstituted 9 to 11 membered heterobicyclyl; or substituted 9 to 11 membered heterobicyclyl. 
     
     
       5. A pharmaceutical composition according to  claim 1 , wherein T 1  is unsubstituted, substituted with one R 5 , two R 5 , one R 6 , two R 6 , or one R 5  and one R 6 . 
     
     
       6. A pharmaceutical composition according to  claim 1 , wherein T 1  is phenyl; pyrrolyl; furyl; thienyl; pyrazolyl; oxazolyl; thiazolyl; pyridyl and N-oxide thereof; pyrimidinyl; indolyl; indolinyl; indazolyl; quinolinyl; isoquinolinyl; benzodioxolyl; dihydrobenzofuryl; dihydrobenzoxazinyl; dihydrobenzodioxinyl; benzodioxanyl; or benzothiazole dioxide. 
     
     
       7. A pharmaceutical composition according to  claim 1 , wherein T 1  is phenyl or pyridyl. 
     
     
       8. A pharmaceutical composition according to  claim 1 , wherein R 5  is oxo (═O), where the ring is at least partially substituted; F; Cl; CN; N(R 7 R 7a ); OR 7 ; C(O)OR 7 ; C(O)N(R 7 R 7a ); N(R 7 )S(O) 2 R 7a ; S(O) 2 N(R 7 R 7a ); S(O) 2 R 7 ; S(O)R 7 ; N(R 7 )C(O)R 7a ; or C 1-6  alkyl, which is optionally substituted with one or more R 8 . 
     
     
       9. A pharmaceutical composition according to  claim 1 , wherein R 7 , R 7a  are independently selected from the group consisting of H; CH 3 ; CH 2 CH 3 ; n-butyl; tert.-butyl; iso-propyl; n-pentyl; isopentyl; neopentyl; 2-ethylbutyl; CF 3 ; CH 2 CH 2 OH; CH 2 CH 2 CH 2 OH; CH 2 C(CH 3 ) 2 CH 2 OH; CH 2 CH 2 OCH 3 ; CH 2 CH 2 NH 2 ; CH 2 CF 3 ; CH 2 CH 2 CF 3 ; CH 2 CH 2 CH 2 CF 3 ; C(CH 3 ) 2 CF 3 ; CH 2 CH 2 NHCH 3 ; CH 2 CH 2 N(CH 3 ) 2 ; CH 2 CH 2 CH 2 N(CH 3 ) 2 ; CH 2 C(O)OH; and CH 2 C(O)N(CH 3 ) 2 . 
     
     
       10. A pharmaceutical composition according to  claim 1 , wherein R 8  is F; Cl; Br; OH; CH 3 ; or CH 2 CH 3 . 
     
     
       11. A pharmaceutical composition according to  claim 1 , wherein R 5  is oxo (═O), where the ring is at least partially substituted; F; Cl; NH 2 ; NH(CH 3 ); N(CH 3 ) 2 ; NH(CH 2 ) 2 OH; N((CH 2 ) 2 OH) 2 ; OH; OCH 3 ; OCF 3 ; OCH(CH 3 ) 2 ; CH 2 OH; CH 2 OCH 3 ; CH 2 Br; CH 3 ; CH 2 CH 3 ; CH(CH 3 ) 2 ; C(CH 3 ) 3 ; CF 3 ; C(O)OH; C(O)OCH 3 ; C(O)OCH 2 CH 3 ; C(O)NH 2 ; C(O)NH(CH 3 ); C(O)(CH 3 ) 2 ; C(O)NHCH 2 CH 3 ; C(O)N(CH 3 )CH 2 CH 3 ; C(O)NHCH 2 CH 2 OH; C(O)N(CH 3 )CH 2 CH 2 OH; C(O)NHCH 2 CH 2 OCH 3 ; C(O)N(CH 3 )CH 2 CH 2 OCH 3 ; C(O)NHCH 2 CH 2 NH 2 ; C(O)N(CH 3 )CH 2 CH 2 NH 2 ; C(O)NHCH 2 CH 2 NHCH 3 ; C(O)N(CH 3 )CH 2 CH 2 NHCH 3 ; C(O)NHCH 2 CH 2 N(CH 3 ) 2 ; C(O)N(CH 3 )CH 2 CH 2 N(CH 3 ) 2 ; HNC(O)H 3 ; S(O) 2 CH 3 ; S(O)CH 3 ; S(O) 2 NH 2 ; S(O) 2 NHC(CH 3 ) 3 ; S(O) 2 NHCH 2 CH(CH 2 CH 3 ) 2 ; S(O) 2 NH(CH 2 ) 2 OH; S(O) 2 NH(CH 2 ) 2 CF 3 ; S(O) 2 NH(CH 2 ) 3 CF 3 ; S(O) 2 NH(CH 2 ) 3 OH; S(O) 2 NHCH 2 C(CH 3 ) 2 CH 2 OH; S(O) 2 NH(CH 2 ) 2 OCH 3 ; or NHS(O) 2 CH 3 . 
     
     
       12. A pharmaceutical composition according to  claim 1 , wherein R 6  is S(O) 2 N(R 9 R 9a ); N(R 9 )S(O) 2 R 9a ; S(O) 2 R 9 ; OR 9 ; or SR 9 . 
     
     
       13. A pharmaceutical composition according to  claim 1 , wherein R 6  is S(O) 2 N(R 9c R 9d ); N(R 9d )S(O) 2 R 9c ; S(O) 2 R 9c ; or OR 9c . 
     
     
       14. A pharmaceutical composition according to  claim 1 , wherein R 9c  is T 2 ; CH 2 -T 2 ; or C 1-4  alkyl-T 2 . 
     
     
       15. A pharmaceutical composition according to  claim 1 , wherein R 9d  is H or methyl. 
     
     
       16. A pharmaceutical composition according to  claim 1 , wherein T 2  is phenyl; naphthyl; C 3-4  cycloalkyl; or 4 to 7 membered heterocyclyl, wherein T 2  is optionally substituted with up to three R 11 . 
     
     
       17. A pharmaceutical composition according to  claim 1 , wherein T 2  is azetidinyl; imidazolidinyl; pyrrolidinyl; piperidinyl; piperizinyl; isoindolinyl; oxazolyl; dihydroisoquinolinyl; morpholinyl; pyranyl; azepanyl; azetidinyl; thiamorpholine dioxide; cyclopropyl; cyclobutyl; cyclopentyl; cyclohexyl; cycloheptyl; phenyl; or naphthyl. 
     
     
       18. A pharmaceutical composition according to  claim 1 , wherein R 11  is oxo (═O), where the ring is at least partially saturated; F; Cl; CH 3 ; CH 2 CH 3 ; CH 2 CH 2 CH 3 ; CH(CH 3 ) 2 ; CF 3 ; OH; OCH 3 ; OCF 3 ; NH 2 ; NHCH 3 ; N(CH 3 ) 2 . 
     
     
       19. A pharmaceutical composition according to  claim 1  of formula (Ia) 
       
         
           
           
               
               
           
         
         wherein 
         X has the meaning as indicated in  claim 1 ; 
         A is CH; or N; 
         R 14  is H; or R 5 ; 
         R 13  is H; R 5 ; or R 6 . 
       
     
     
       20. A pharmaceutical composition according to  claim 19 , wherein R 13  is R 5  or R 6 . 
     
     
       21. A pharmaceutical composition according to  claim 19 , wherein R 13  is H; OH; or OCH 3 . 
     
     
       22. A pharmaceutical composition according to  claim 1  wherein the compound of formula (I) or pharmaceutically acceptable salt thereof is selected from the group consisting of:
 3-(2-Amino-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-N-(2-hydroxy-ethyl)-benzenesulfonamide; 
 6-(5-Methanesulfonyl-pyridin-3-yl)-[1,2,4]triazolo[1,5-a]pyridin-2-ylamine; 
 5-(2-Amino-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-pyridine-3-sulfonic acid butylamide; 
 5-(2-Amino-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-2-methoxy-phenol; 
 5-(2-Amino-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-pyridine-3-sulfonic acid tert-butylamide; 
 5-(2-Amino-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-pyridine-3-sulfonic acid benzylamide; 
 5-(2-Amino-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-pyridine-3-sulfonic acid (2-ethyl-butyl)-amide; 
 5-(2-Amino-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-pyridine-3-sulfonic acid (4-chloro-phenyl)-amide; 
 5-(2-Amino-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-pyridine-3-sulfonic acid (3,5-bis-trifluoromethyl-phenyl)-amide; 
 5-(2-Amino-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-pyridine-3-sulfonic acid (4-fluoro-phenyl)-amide; 
 6-(3-Methanesulfonyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-ylamine; 
 6-(3,4-dimethoxyphenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-amine; 
 3-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-N-(2-aminoethyl)benzenesulfonamide; 
 6-(3-isopropoxy-4-methoxyphenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-amine; 
 4-(2-Amino-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-2-methoxyphenol; 
 3-(2-Amino-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-N-butylbenzenesulfonamide; 
 4,4,4-Trifluorobutane-1-sulfonic acid [5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-pyridin-3-yl]amide; 
 N-[5-(2-Amino-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-pyridin-3-yl]-3-trifluoromethylbenzenesulfonamide HCl salt; 
 N-[5-(2-Amino-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-pyridin-3-yl]-2-trifluoromethylbenzenesulfonamide HCl salt; 
 N-[5-(2-Amino-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-pyridin-3-yl]-4-trifluoromethylbenzenesulfonamide HCl salt; 
 Naphthalene-2-sulfonic acid [5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-pyridin-3-yl]-amide HCl salt; 
 N-[5-(2-Amino-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-pyridin-3-yl]-4-isopropylbenzenesulfonamide HCl salt; 
 Naphthalene-1-sulfonic acid [5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-pyridin-3-yl]-amide HCl salt; 
 N-[5-(2-Amino-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-pyridin-3-yl]-4-chlorobenzenesulfonamide HCl salt; 
 6-(3,4-Dimethoxyphenyl)-8-chloro-[1,2,4]triazolo[1,5-a]pyridine-2-ylamine; 
 N-[5-(2-Amino-[1,2,4]triazolo[1,5-a]pyridin-6-yl)pyridine-3-yl]-3-trifluoromethoxybenzenesulfonamide HCl; 
 N-[5-(2-Amino-[1,2,4]triazolo[1,5-a]pyridin-6-yl)pyridine-3-yl]-C-(2-trifluoromethylphenyl)methanesulfonamide HCl; 
 N-[5-(2-Amino-[1,2,4]triazolo[1,5-a]pyridin-6-yl)pyridine-3-yl]-C-(4-trifluoromethylphenyl)methanesulfonamide HCl; 
 N-[5-(2-Amino-[1,2,4]triazolo[1,5-a]pyridin-6-yl)pyridine-3-yl]-C-(4-chlorophenyl)methanesulfonamide HCl; 
 N-[5-(2-Amino-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-pyridin-3-yl]-3,5-bis-trifluoromethylbenzenesulfonamide; 
 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-N-(4-(trifluoromethyl)phenyl)pyridine-3-sulfonamide; 
 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-N-(2-(trifluoromethyl)phenyl)pyridine-3-sulfonamide; 
 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-N-(3-(trifluoromethyl)phenyl)pyridine-3-sulfonamide; 
 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-N-methyl-N-(3-(trifluoromethyl)phenyl)pyridine-3-sulfonamide; 
 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-N-(4-(trifluoromethoxy)phenyl)pyridine-3-sulfonamide; 
 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-N-phenylpyridine-3-sulfonamide; 
 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-N-(3-(trifluoromethoxy)phenyl)pyridine-3-sulfonamide; 
 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-N-(3-(1,1,2,2-tetrafluoroethoxy)phenyl)pyridine-3-sulfonamide; 
 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-N-(3-(difluoromethoxy)phenyl)pyridine-3-sulfonamide; 
 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-N-(4-(difluoromethoxy)phenyl)pyridine-3-sulfonamide; 
 6-(5-(trifluoromethyl)pyridin-3-yl)-[1,2,4]triazolo[1,5-a]pyridin-2-amine; 
 6-(4-isopropoxy-3-methoxyphenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-amine; 
 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridine-6-yl)-N-(2-methyl-1-(pyrrolidin-1-yl)propan-2-yl)pyridine-3-sulfonamide; 
 6-(5-(4-fluoropiperidin-1-ylsulfonyl)pyridine-3-yl)-[1,2,4]triazolo[1,5-a]pyridine-2-amine; 
 6-(5-(4-methylpiperizin-1-ylsulfonyl)pyridine-3-yl)-[1,2,4]triazolo[1,5-a]pyridine-2-amine; 
 2-(5-(2-amino-[1,2,4]triazolo[1,5-a]pyridine-6-yl)pyridine-3-sulfoamido)-N,N-dimethylacetamide; 
 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridine-6-yl)-N-(2-(oxoimidazolidin-1-yl)ethyl)pyridine-3-sulfonamide; 
 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridine-6-yl)-N-(2-(dimethylamino)ethyl)-N-methylpyridine-3-sulfonamide; 
 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridine-6-yl)-N-(3-(dimethylamino)propyl)pyridine-3-sulfonamide; 
 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridine-6-yl)-N-butyl-N-methylpyridine-3-sulfonamide; 
 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridine-6-yl)-N-isopentylpyridine-3-sulfonamide; 
 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridine-6-yl)-N-(cyclopropylmethyl)pyridine-3-sulfonamide; 
 6-(5-isoindolin-2-ylsulfonyl)pyridine-3-yl)-[1,2,4]triazolo[1,5-a]pyridin-2-amine; 
 6-(5-piperazin-1-ylsulfonyl)pyridine-3-yl)-[1,2,4]triazolo[1,5-a]pyridin-2-amine; 
 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-N-benzyl-N-methylpyridine-3-sulfonamide; 
 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-N-(2,4-dimethyloxazol-5-yl)methyl)pyridine-3-sulfonamide; 
 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-N-benzyl-N-butylpyridine-3-sulfonamide; 
 6-(5-(3,4-dihydroisoquinolin-2(1H)-ylsulfonyl)pyridine-3-yl-[1,2,4]triazolo[1,5-a]pyridin-amine; 
 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-N-(2,3-dichlorobenzyl)-N-methylpyridine-3-sulfonamide; 
 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-N-cyclopropyl-N-(2-fluorobenzyl)pyridine-3-sulfonamide; 
 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-N-(2-phenylpropan-2-yl)pyridine-3-sulfonamide; 
 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-N-(2-(4-fluorophenyl)propan-2-yl)pyridine-3-sulfonamide; 
 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-N-(4-fluorobenzyl)pyridine-3-sulfonamide; 
 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-N,N-diethylpyridine-3-sulfonamide; 
 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-N-(1,1,1-trifluoro-2-methylpropan-2-yl)pyridine-3-sulfonamide; 
 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-6-yl)pyridine-3-sulfonamide; 
 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-N-butylpyridine-3-sulfonamide; 
 6-(5-(morpholinosulfonyl)pyridin-3-yl)-[1,2,4]triazolo[1,5-a]pyridin-2-amine; 
 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-N-(3,3,3-trifluoropropyl)pyridine-3-sulfonamide; 
 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-N,N-dimethylpyridine-3-sulfonamide; 
 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-N-neopentylpyridine-3-sulfonamide; 
 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-N-cyclopentylpyridine-3-sulfonamide; 
 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-N-(3,4-dichlorobenzyl)pyridine-3-sulfonamide; 
 3-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-N-(2-(dimethylamino)ethyl)benzenesulfonamide; 
 3-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-N-(2-(dimethylamino)ethyl)-N-methylbenzenesulfonamide; 
 3-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-N-tert-butylbenzenesulfonamide; 
 2-(3-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-6-yl)phenylsulfonamido)acetic acid; 
 3-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-N-(3-(dimethylamino)propyl)benzenesulfonamide; 
 6-(5-chloropyridin-3-yl)-[1,2,4]triazolo[1,5-a]pyridin-2-amine; 
 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-N-cyclopropylpyridine-3-sulfonamide; 
 6-(5-(pyrrolidin-1-ylsulfonyl)pyridin-3-yl)-[1,2,4]triazolo[1,5-a]pyridin-2-amine; 
 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-N-tert-butyl-N-methylpyridine-3-sulfonamide; 
 6-(5-(piperidin-1-ylsulfonyl)pyridin-3-yl)-[1,2,4]triazolo[1,5-a]pyridin-2-amine; 
 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-N-isobutylpyridine-3-sulfonamide; 
 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-N-isopropylpyridine-3-sulfonamide; 
 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-N-(2,3-dichlorobenzyl)pyridine-3-sulfonamide; 
 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-N-propylpyridine-3-sulfonamide; 
 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-N-(2,2,2-trifluoroethyl)pyridine-3-sulfonamide; 
 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-N-cyclohexylpyridine-3-sulfonamide; 
 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-N-(tetrahydro-2H-pyran-4-yl)pyridine-3-sulfonamide; 
 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-N-((tetrahydro-2H-pyran-4-yl)methyl)pyridine-3-sulfonamide; 
 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-N-(4-hydroxycyclohexyl)pyridine-3-sulfonamide; 
 6-(5-(4,4-difluoropiperidin-1-ylsulfonyl)pyridin-3-yl)-[1,2,4]triazolo[1,5-a]pyridin-2-amine; 
 6-(5-(azepan-1-ylsulfonyl)pyridin-3-yl)-[1,2,4]triazolo[1,5-a]pyridin-2-amine; 
 6-(5-(azetidin-1-ylsulfonyl)pyridin-3-yl)-[1,2,4]triazolo[1,5-a]pyridin-2-amine; 
 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-N-(cyclobutylmethyl)pyridine-3-sulfonamide; 
 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-N-ethylpyridine-3-sulfonamide; 
 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-N-methylpyridine-3-sulfonamide; 
 6-(3,4-dimethoxyphenyl)-8-fluoro-[1,2,4]triazolo[1,5-a]pyridin-2-amine; 
 6-(3,4-dimethoxyphenyl)-8-methyl-[1,2,4]triazolo[1,5-a]pyridin-2-amine; 
 6-(5-(benzylsulfonyl)pyridin-3-yl)-[1,2,4]triazolo[1,5-a]pyridin-2-amine; 
 6-(5-(tert-Butylsulfonyl)pyridin-3-yl)-[1,2,4]triazolo[1,5-a]pyridin-2-amine; 
 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-N-ethyl-N-methylpyridine-3-sulfonamide; 
 5-(2-amino-8-fluoro-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-N-tert-butylpyridine-3-sulfonamide; 
 6-(5-isobutoxypyridin-3-yl)-[1,2,4]triazolo[1,5-a]pyridin-2-amine; 
 6-(5-(benzyloxy)pyridin-3-yl)-[1,2,4]triazolo[1,5-a]pyridin-2-amine; 
 6-(5-phenoxypyridin-3-yl)-[1,2,4]triazolo[1,5-a]pyridin-2-amine; 
 6-(5-(neopentyloxy)pyridin-3-yl)-[1,2,4]triazolo[1,5-a]pyridin-2-amine; 
 6-(5-(neopentylsulfonyl)pyridin-3-yl)-[1,2,4]triazolo[1,5-a]pyridin-2-amine; 
 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-N-(cyclopentylmethyl)pyridine-3-sulfonamide; 
 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-N-(cycloheptylmethyl)pyridine-3-sulfonamide; 
 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-N-(3-isopropylphenyl)pyridine-3-sulfonamide; 
 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-N-(2-fluorophenyl)pyridine-3-sulfonamide; 
 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-N-(4-isopropylphenyl)pyridine-3-sulfonamide; 
 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-N-(2-methoxyphenyl)pyridine-3-sulfonamide; 
 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-N-(2,4-difluorophenyl)pyridine-3-sulfonamide; 
 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-N-tert-butylnicotinamide; 
 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-N-(4-methoxyphenyl)pyridine-3-sulfonamide; 
 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-N-(3-fluorophenyl)pyridine-3-sulfonamide; 
 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-N-(3,4-difluorophenyl)pyridine-3-sulfonamide; 
 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-N-(2-isopropylphenyl)pyridine-3-sulfonamide; 
 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-N-(3,5-difluorophenyl)pyridine-3-sulfonamide; 
 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-N-(3-methoxyphenyl)pyridine-3-sulfonamide; 
 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-N-(2,3-difluorophenyl)pyridine-3-sulfonamide; 
 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-N-(1-methylcyclobutyl)pyridine-3-sulfonamide; 
 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-N-(2-aminoethyl)pyridine-3-sulfonamide; 
 5-(2-amino-8-fluoro-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-N-methylpyridine-3-sulfonamide; 
 5-(2-amino-8-fluoro-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-N-isopropylpyridine-3-sulfonamide; 
 5-(2-amino-8-fluoro-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-N-propylpyridine-3-sulfonamide; 
 6-(5-(azetidin-1-ylsulfonyl)pyridin-3-yl)-8-fluoro-[1,2,4]triazolo[1,5-a]pyridin-2-amine; 
 5-(2-amino-8-fluoro-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-N-(2,2,2-trifluoroethyl)pyridine-3-sulfonamide; 
 5-(2-amino-8-fluoro-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-N-ethyl-N-methylpyridine-3-sulfonamide; 
 8-fluoro-6-(3-(methylsulfonyl)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-amine; 
 6-(6-amino-5-(trifluoromethyl)pyridin-3-yl)-[1,2,4]triazolo[1,5-a]pyridin-2-amine; 
 5-(3-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-6-yl)phenylsulfonamido)pentanoic acid; 
 4-(3-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-6-yl)phenylsulfonamido)butanoic acid; 
 6-(5-(benzylthio)pyridin-3-yl)-[1,2,4]triazolo[1,5-a]pyridin-2-amine; 
 8-fluoro-6-(5-(trifluoromethyl)pyridin-3-yl)-[1,2,4]triazolo[1,5-a]pyridin-2-amine; 
 6-(4-fluorophenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-amine hydrochloride; 
 6-(3-methoxyphenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-amine hydrochloride; 
 6-(3,4,5-trimethoxyphenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-amine hydrochloride; 
 6-m-tolyl-[1,2,4]triazolo[1,5-a]pyridin-2-amine; 
 3-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-6-yl)benzonitrile; 
 6-(3-chlorophenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-amine; 
 6-phenyl-[1,2,4]triazolo[1,5-a]pyridin-2-amine; 
 6-(2-methoxyphenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-amine; 
 6-(3-(ethylamino)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-amine; 
 4-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-6-yl)benzamide; 
 6-(pyrimidin-5-yl)-[1,2,4]triazolo[1,5-a]pyridin-2-amine hydrochloride; 
 6-(1-methyl-1H-pyrazol-4-yl)-[1,2,4]triazolo[1,5-a]pyridin-2-amine hydrochloride; 
 3-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-6-yl)phenol; 
 6-(3-(trifluoromethyl)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-amine hydrochloride; 
 6-(benzo[d][1,3]dioxol-5-yl)-[1,2,4]triazolo[1,5-a]pyridin-2-amine hydrochloride; 
 6-(3,4-dimethoxyphenyl)-7-methyl-[1,2,4]triazolo[1,5-a]pyridin-2-amine hydrochloride; 
 6-(3,4-difluorophenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-amine hydrochloride; 
 6-(3-fluorophenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-amine hydrochloride; 
 6-(4-methoxyphenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-amine; 
 N-(3-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-6-yl)phenyl)acetamide; 
 6-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-[1,2,4]triazolo[1,5-a]pyridin-2-amine; 
 3-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-6-yl)benzenesulfonamide; 
 4-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-6-yl)benzenesulfonamide; 
 3-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-6-yl)benzoic acid; 
 6-(pyridin-4-yl)-[1,2,4]triazolo[1,5-a]pyridin-2-amine; 
 6-(1H-pyrazol-3-yl)-[1,2,4]triazolo[1,5-a]pyridin-2-amine; 
 6-(thiophen-2-yl)-[1,2,4]triazolo[1,5-a]pyridin-2-amine; and 
 6-(1H-pyrazol-4-yl)-[1,2,4]triazolo[1,5-a]pyridin-2-amine. 
 
     
     
       23. A pharmaceutical composition according to  claim 1  in combination with one or more other pharmaceutical compositions. 
     
     
       24. A pharmaceutical composition according to  claim 23 , comprising one or more additional compounds or pharmaceutically acceptable salts thereof selected from the group consisting of compounds of formula (I) or a pharmaceutically acceptable salt thereof as defined in  claim 1  and not being the first compound; other P13K inhibitors, steroids, leukotriene antagonists, antihistamines, cyclosporine or rapamycin. 
     
     
       25. A pharmaceutical composition according to  claim 1 , wherein:
 R 1  and R 2  are independently H or CH 3 ; 
 R 3  is H, CH 3  or halogen; 
 T 1  is unsubstituted phenyl; substituted phenyl; unsubstituted 4 to 7 membered heterocyclyl; substituted 4 to 7 membered heterocyclyl; unsubstituted 9 to 11 membered heterobicyclyl; or substituted 9 to 11 membered heterobicyclyl; 
 R 5  is oxo (═O), where the ring is at least partially substituted; F; Cl; CN; N(R 7 R 7a ); OR 7 ; 
 C(O)OR 7 ; C(O)N(R 7 R 7a ); N(R 7 )S(O) 2 R 7a ; S(O) 2 N(R 7 R 7a ); S(O) 2 R 7 ; S(O)R 7 ; N(R 7 )C(O)R 7a ; or C 1-6  alkyl, which is optionally substituted with one or more R 8 ; 
 R 7 , R 7a  are independently selected from the group consisting of H; CH 3 ; CH 2 CH 3 ; n-butyl; tert.-butyl; iso- propyl; n-pentyl; isopentyl; neopentyl; 2-ethylbutyl; CF 3 ; CH 2 CH 2 OH; CH 2 CH 2 CH 2 OH; CH 2 C(CH 3 ) 2 CH 2 OH; CH 2 CH 2 OCH 3 ; CH 2 CH 2 NH 2 ; CH 2 CF 3 ; CH 2 CH 2 CF 3 ; CH 2 CH 2 CH 2 CF 3 ; C(CH 3 ) 2 CF 3 ; CH 2 CH 2 NHCH 3 ; CH 2 CH 2 N(CH 3 ) 2 ; CH 2 CH 2 CH2N(CH 3 )2; CH 2 C(O)OH; and CH 2 C(O)N(CH 3 ) 2 ; 
 R 8  is F; Cl; Br; OH; CH 3 ; or CH 2 CH 3 ; 
 R 6  is S(O) 2 N(R 9 R 9a ); N(R 9 )S(O) 2 R 9a ; S(O) 2 R 9 ; OR 9 ; or SR 9 ; 
 R 9c  is T 2 ; CH 2 -T 2 ; or C 1-4  alkyl-T 2 ; 
 R 9d  is H or methyl; 
 T 2  is phenyl; naphthyl; C 3-4  cycloalkyl; or 4 to 7 membered heterocyclyl, wherein T 2  is optionally substituted with up to three R 11 ; and 
 R 11  is oxo (═O), where the ring is at least partially saturated; F; Cl; CH 3 ; CH 2 CH 3 ; CH 2 CH 2 CH 3 ; CH(CH 3 ) 2 ; CF 3 ; OH; OCH 3 ; OCF 3 ; NH 2 ; NHCH 3 ; or N(CH 3 ) 2 . 
 
     
     
       26. A pharmaceutical composition according to  claim 25 , wherein:
 T 1  is unsubstituted, substituted with one R 5 , two R 5 , one R 6 , two R 6 , or one R 5  and one R 6 ; and 
 R 6  is S(O) 2 N(R 9c R 9d ); N(R 9d )S(O) 2 R 9c ; S(O) 2 R 9c ; or OR 9c . 
 
     
     
       27. A pharmaceutical composition according to  claim 25 , wherein:
 T 1  is phenyl; pyrrolyl; furyl; thienyl; pyrazolyl; oxazolyl; thiazolyl; pyridyl and N-oxide thereof; pyrimidinyl; indolyl; indolinyl; indazolyl; quinolinyl; isoquinolinyl; benzodioxolyl; dihydrobenzo furyl; dihydrobenzoxazinyl; dihydrobenzodioxinyl; benzodioxanyl; or benzothiazole dioxide; 
 R 5  is oxo (═O), where the ring is at least partially substituted; F; Cl; NH 2 ; NH(CH 3 ); N(CH 3 ) 2 ; NH(CH 2 ) 2 OH; N((CH 2 ) 2 OH) 2 ; OH; OCH 3 ; OCF 3 ; OCH(CH 3 ) 2 ; CH 2 OH; CH 2 OCH 3 ; CH 2 Br; CH 3 ; CH 2 CH 3 ; CH(CH 3 ) 2 ; C(CH 3 ) 3 ; CF 3 ; C(O)OH; C(O)OCH 3 ; C(O)OCH 2 CH 3 ; C(O)NH 2 ; C(O)NH(CH 3 ); C(O)(CH 3 ) 2 ; C(O)NHCH 2 CH 3 ; C(O)N(CH 3 )CH 2 CH 3 ; C(O)NHCH 2 CH 2 OH; C(O)N(CH 3 )CH 2 CH 2 OH; C(O)NHCH 2 CH 2 OCH 3 ; C(O)N(CH 3 )CH 2 CH 2 OCH 3 ; C(O)NHCH 2 CH 2 NH 2 ; C(O)N(CH 3 )CH 2 CH 2 NH 2 ; C(O)NHCH 2 CH 2 NHCH 3 ; C(O)N(CH 3 )CH 2 CH 2 NHCH 3 ; C(O)NHCH 2 CH 2 N(CH 3 ) 2 ; C(O)N(CH 3 )CH 2 CH 2 N(CH 3 ) 2 ; HNC(O)H 3 ; S(O) 2 CH 3 ; S(O)CH 3 ; S(O) 2 NH 2 ; S(O) 2 NHC(CH 3 ) 3 ; S(O) 2 NHCH 2 CH(CH 2 CH 3 ) 2 ; S(O) 2 NH(CH 2 ) 2 OH; S(O) 2 NH(CH 2 ) 2 CF 3 ; S(O) 2 NH(CH 2 ) 3 CF 3 ; S(O) 2 NH(CH 2 ) 3 OH; S(O) 2 NHCH 2 C(CH 3 ) 2 CH 2 OH; S(O) 2 NH(CH 2 ) 2 OCH 3 ; or NHS(O) 2 CH 3 ; and 
 T 2  is imidazolidinyl; pyrrolidinyl; piperidinyl; piperizinyl; isoindolinyl; oxazolyl; dihydroisoquinolinyl; morpholinyl; pyranyl; azepanyl; azetidinyl; thiamorpholine dioxide; cyclopropyl; cyclobutyl; cyclopentyl; cyclohexyl; cycloheptyl; phenyl; or naphthyl. 
 
     
     
       28. A pharmaceutical composition according to  claim 27 , wherein T 1  is phenyl or pyridyl.
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